This invention relates to a method for the preparation of oxydiphthalic anhydrides. The products are useful chemical intermediates for the further preparation of various compounds such as the corresponding dicarboxylic acids and the various derivatives thereof, including for example, the salts, esters, acyl halides, amides, imides and the like. The oxydiphthalic anhydrides are particularly useful as monomers in the preparation of polyimides, for example by polycondensation with a suitable diamine, such as ethylenediamine or phenylenediamine.
Various methods for the preparation of oxydiphthalic anhydrides have been described in the chemical literature. One such method, shown to be useful in the preparation of oxydiphthalic acids and anhydrides, involves the oxidation of tetramethyl diphenyl ethers. See Kolesnikov, G. S. et al, Vysokomol. Soyed, A9, 612-18 (1967); Marvel, C. S. et al, J. Am. Chem. Soc., 80, 1197 (1958); and Latrova, Z. N. et al, Volokna Sin. Polim., 15-24 (1970).
Three Japanese patents assigned to Mitsui Toatsu Chemicals, Inc describe preparations based reactions of substituted phthalic anhydrides. Japanese Patent Document 80/136,246 (Chem. Abst. 95:42680) teaches the coupling of 4-nitrophthalic anhydride in the presence of sodium nitrite or potassium nitrate to form oxydiphthalic anhydride. Japanese Patent Document 80/122, 738 (Chem. Abst. 94.83799) discloses the reaction of 4-halophthalic acid or anhydride with an alkali metal hydroxide to yield oxydiphthalic anhydride. In Japanese Patent Document 80/127, 343 (Chem. Abst. 94:191942) the reaction of 4-halo-phthalic anhydride, Na.sub.2 CO.sub.3 and NaNO.sub.2 in dimethyl sulfoxide to form 4,4"-dihydroxydiphthalylic anhydride is described.
German Patent 2,416,594 (1975) discloses the coupling of 3-nitrophthalic anhydride in the presence of metal nitrites, such as sodium nitrite to form oxydiphthalic anhydride.
Markezich, R. L. and Zamek, O. S., J. Org. Chem., 42, 3431, (1977) describe reaction of 4-nitrophthalimide with potassium fluoride in dimethylsulfoxide to form the corresponding oxydiphthalimide which may be converted by hydrolysis to form the acid and ring closure to form the dianhydride.